EP2911530B1 - Eingekapselte bittere peptide, verfahren zum einkapseln bittere peptide und nahrungszusammensetzungen mit verkapselten bitteren peptiden - Google Patents

Eingekapselte bittere peptide, verfahren zum einkapseln bittere peptide und nahrungszusammensetzungen mit verkapselten bitteren peptiden Download PDF

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EP2911530B1
EP2911530B1 EP13779563.9A EP13779563A EP2911530B1 EP 2911530 B1 EP2911530 B1 EP 2911530B1 EP 13779563 A EP13779563 A EP 13779563A EP 2911530 B1 EP2911530 B1 EP 2911530B1
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Prior art keywords
bitter peptides
protein
peptides
encapsulated
bitter
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French (fr)
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EP2911530A2 (de
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Elodie SOUSSAN
Françoise MAYNARD
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Societe des Produits Nestle SA
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Nestec SA
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/18—Peptides; Protein hydrolysates
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • A23P10/35—Encapsulation of particles, e.g. foodstuff additives with oils, lipids, monoglycerides or diglycerides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/1703—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
    • A61K38/1709—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A61K9/5107—Excipients; Inactive ingredients
    • A61K9/5123—Organic compounds, e.g. fats, sugars
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present disclosure relates generally to encapsulated bitter peptides, methods of encapsulating bitter peptides, and nutritional compositions including encapsulated bitter peptides. More specifically, the present disclosure is directed to bitter peptides encapsulated in a lipid matrix, wherein said lipid matrix is an organogel.
  • Protein hydrolyzates are commercially used specialized nutrition products for addressing specific consumers benefits and/or needs, such as for critical patients, and for prevention and management of allergy. Many such specialized nutrition products include proteins that are pre-digested by hydrolysis with an enzyme. However, hydrolysis may form hydrophobic fragments of proteins that have a bitter taste. See, e.g., Leksrisompong, P.P., "Characterization of flavor of whey protein hydrolysates," J. Agric. Food Chem., 58(10):6318-6327 (2010 ). Nevertheless, peptides not only contribute to the nutritional profile of the composition but also help stabilize the emulsion in the composition.
  • bitter peptides for taste-masking purposes is known from WO2010/039036 , WO2008/130236 , EP1897451 and JPH0283031 .
  • a nutritional composition includes bitter peptides encapsulated in a structure, wherein said structure is anorganogel.
  • the structure is an organogel comprising an oil and a gelator, for example distilled monoglycerides.
  • a method of encapsulating bitter peptides includes the steps of forming an emulsion comprising a water phase containing protein hydrolysate and an oil phase comprising at least one of an oil or a melted fat; and adding a gelator to the emulsion to form an organogel after the bitter peptides from the protein hydrolysate migrate selectively into oil droplets in the oil phase, the addition of the gelator entrapping the bitter peptides in the organogel.
  • the protein hydrolysate is a dairy based protein hydrolysate.
  • the dairy based protein hydrolysate protein is a whey protein hydrolysate.
  • the protein hydrolysate is a vegetable based protein hydrolysate, such as pea and/or soy protein hydrolysate.
  • the method includes hydrolysis of protein to form a solution comprising the protein hydrolysate in a water phase, the bitter peptides being selectively entrapped in the organogel in line such that the emulsion is formed after the hydrolysis directly in the solution comprising the protein hydrolysate.
  • the hydrolysis forms non-bitter peptides, and at least a portion of the non-bitter peptides are not entrapped in the oil phase.
  • the water phase contains about 5% to about 50% of the protein hydrolysate by weight, preferably about 5% to about 25%, such as about 5% to about 15% of the protein hydrolysate by weight.
  • bitter peptides encapsulated in a structure wherein said structure is an organogel.
  • a method of providing nutrition includes administering a nutritional composition comprising bitter peptides from protein hydrolysate, the bitter peptides encapsulated in a structure, wherein said structure is an organogel.
  • An advantage of the present disclosure is to provide encapsulated bitter peptides.
  • Another advantage of the present disclosure is to provide improved nutritional compositions.
  • Still another advantage of the present disclosure is to provide nutritional compositions that have acceptable organoleptic properties.
  • Yet another advantage of the present disclosure is to hide bitter peptides to taste receptors by encapsulating the peptides.
  • Still another advantage of embodiments of the present disclosure is to encapsulate bitter peptides in line, such that hydrophobic interactions encapsulate the bitter peptides directly in the water phase after inactivation of the enzyme, or near line.
  • Yet another advantage of the present disclosure is to selectively encapsulate bitter peptides such that at least a portion of the peptides that assist emulsion stability are not encapsulated.
  • FIG. 1 is a graph showing results from tastings of encapsulated bitter peptides in accordance with embodiments of the present disclosure.
  • bitter peptides are any hydrophobic peptide formed by hydrolysis of protein.
  • the bitter peptides include peptides that bind to the human bitter receptors (for examples T2Rs).
  • the bitter peptides can be formed by hydrolysis of a dietary protein. Pre-hydrolysed proteins are generally more easily digested and absorbed by the gastro-intestinal tract, and have reduced allergenic potential.
  • the hydrolysate of any suitable dietary protein may be used, for example animal proteins, such as milk protein, meat protein and egg protein; or vegetable proteins, such as soy protein, wheat protein, rice protein, pea protein, corn protein, canola protein, oat protein, potato protein, peanut protein, and any proteins derived from beans, buckwheat or lentils.
  • animal proteins such as milk protein, meat protein and egg protein
  • vegetable proteins such as soy protein, wheat protein, rice protein, pea protein, corn protein, canola protein, oat protein, potato protein, peanut protein, and any proteins derived from beans, buckwheat or lentils.
  • Milk proteins, such as casein and whey, and soy proteins may be preferred for some applications.
  • the protein is a milk protein or a milk protein fraction
  • the protein may be, for example, sweet whey, acid whey, ⁇ -lactalbumin, ⁇ -lactoglobulin, bovine serum albumin, acid casein, caseinates, ⁇ -casein, ⁇ -casein and/or ⁇ -casein.
  • sweet whey acid whey
  • ⁇ -lactalbumin ⁇ -lactoglobulin
  • bovine serum albumin bovine serum albumin
  • acid casein caseinates
  • ⁇ -casein ⁇ -casein and/or ⁇ -casein.
  • hydrolysate from a combination of different proteins may be used.
  • Protein hydrolysates can be obtained as a commercial raw material powder or can be produced by hydrolysis of protein, e.g. enzymatic hydrolysis of protein.
  • protein hydrolysates may be produced by hydrolysis of whey protein in water using, proteolitic enzymes.
  • Processes and enzymes for the preparation of protein hydrolysates for food applications are well-known in the art.
  • One example of a process for preparation of protein hydrolysates is described in US5,039,532 .
  • the peptides may be produced by hydrolyzing protein as desired and as known in the art.
  • protein hydrolysate e.g. a whey protein hydrolysate
  • the protein may be obtained already hydrolyzed.
  • encapsulating bitter peptides masked the bitterness relative to un-encapsulated bitter peptides from protein hydrolysates. Without wishing to be bound to any theory, it is believed that the encapsulated bitter peptides reduce undesirable taste of a composition in which they are included because the hydrophobic matrix in which they are encapsulated blocks the bitter peptides from taste receptors.
  • an organogel is a substantially dilute system which exhibits no flow when in the steady-state and is a non-crystalline, non-glassy solid material. These solid materials are composed of a liquid organic phase (e.g vegetable oil) entrapped in and/or physically attached to a three-dimensional network.
  • an organogel can comprise macromolecules interconnected by either strong chemical bonds, such as the bonds of cross-linked polymers, or weaker bonds, such as non-covalent interactions.
  • gelators e.g. monoglyceride
  • an emulsion can be formed.
  • the emulsion is formed after protein hydrolysis directly in the water phase after inactivation of the enzyme.
  • the emulsion can comprise a water phase containing the protein hydrolysate and also comprise an oil phase containing oil and/or melted fat.
  • protein hydrolysate such as whey protein hydrolysate
  • the water phase can comprise about 5% to about 50% of the protein hydrolysate by weight, preferably about 5% to about 25%, such as about 5% to about 15% of the protein hydrolysate by weight.
  • the bitter peptides can initially be located in the water phase but then can migrate inside the oil droplets by hydrophobic interactions. For example, stirring, such as for about 30 minutes, can assist the bitter peptides in migrating inside the oil droplets.
  • gelator molecules such as, for example, phytosterols, phospholipids, monoglycerides and combinations thereof, can be added to the emulsion to gel the oil droplets in which the bitter peptides will be entrapped.
  • Suitable gelators include low molecular weight gelators (LMWGs), such as phospholipids, lecithin, monoglyceride, amphiphilic peptides, sorbitan monostearate, mono-, di- and/or triacyglycerols, fatty acids, fatty alcohol, wax and/or phytosterol.
  • LMWGs low molecular weight gelators
  • a gelator can be added to the emulsion to gel the oil droplets.
  • the organogel is formed using only food grade materials and without using any organic solvents.
  • the gelator may be distilled monoglycerides.
  • the organogel can be used to produce a nutritional composition.
  • the oil and/or melted fat are standard ingredients in a nutritional composition in which the organogel that encapsulates the bitter peptides is used.
  • the formulation of the nutritional composition may not need to be altered to include the organogel.
  • at least a portion of the peptides from the protein hydrolysate that are not bitter and/or not hydrophobic are not encapsulated by the organogel.
  • the solid lipid nanoparticles are stabilized by a surfactant.
  • the present disclosure provides nutritional compositions comprising encapsulated bitter peptides produced using any method disclosed herein.
  • the present disclosure also provides a method of administering bitter peptides to an individual comprising the steps of administering to the individual a nutritional composition comprising the bitter peptides in encapsulated form.
  • the present disclosure also provides a method of treating or preventing a condition in an individual in need thereof comprising the steps of administering to the individual a nutritional composition comprising an effective amount of encapsulated bitter peptides.
  • a method of providing nutrition to a person comprises administering to the person a nutritional formulation comprising bitter peptides from protein hydrolysate.
  • the bitter peptides are encapsulated in a structure selected from the group consisting of organogels, liposomes, solid lipid nanoparticles and combinations thereof.
  • the inventive encapsulation system advantageously liberates the encapsulated peptides during digestion so that the bitter taste of the peptides is masked on consumption/administration of the nutritional composition, whilst maintaining the biological properties of the hydrolysate, such that the hydrophobic peptides are still bioavailable.
  • Nutritional compositions comprising the encapsulated bitter peptides may be pharmaceutical formulations, nutritional formulations, dietary supplements, functional foods, beverage products and combinations thereof.
  • the nutritional composition can be for long-term administration (continuous administrations for more than 6 weeks and/or short-term administration (continuous administrations for less than 6 weeks).
  • the nutritional compositions are in a form selected from the group consisting of tablets, capsules, liquids, chewables, soft gels, sachets, powders, syrups, liquid suspensions, emulsions, solutions, or combinations thereof.
  • the nutritional compositions are oral nutritional supplements.
  • the nutritional compositions may also be a source of complete nutrition.
  • Complete nutrition provides types and levels of macronutrients (protein, fats and carbohydrates) and micronutrients to be sufficient to be a sole source of nutrition for the animal to which it is being administered. Patients can receive 100% of their nutritional requirements from such complete nutritional compositions.
  • the nutritional compositions may be a source of incomplete nutrition. Incomplete nutrition does not provide levels of macronutrients (protein, fats and carbohydrates) or micronutrients to be sufficient to be a sole source of nutrition for the animal to which it is being administered. Partial or incomplete nutritional compositions can be used as a nutritional supplement.
  • the nutritional composition can be an infant formula.
  • Nutritional products or “nutritional compositions,” as used herein, are understood to include any number of optional additional ingredients, including conventional food additives (synthetic or natural), for example one or more acidulants, additional thickeners, buffers or agents for pH adjustment, chelating agents, colorants, emulsifies, excipient, flavor agent, mineral, osmotic agents, a pharmaceutically acceptable carrier, preservatives, stabilizers, sugar, sweeteners, texturizers, and/or vitamins.
  • the optional ingredients can be added in any suitable amount.
  • the nutritional products or compositions may be a source of complete nutrition or may be a source of incomplete nutrition.
  • the nutritional compositions can include any number of optional additional ingredients, including conventional food additives (synthetic or natural), for example one or more acidulants, additional thickeners, buffers or agents for pH adjustment, chelating agents, colorants, emulsifiers, excipients, flavor agents, osmotic agents, pharmaceutically acceptable carriers, preservatives, stabilizers, sugar, sweeteners, texturizers, and/or vitamins.
  • the nutritional compositions may contain emulsifiers and stabilizers such as soy lecithin, citric acid esters of mono- and di-glycerides, and the like.
  • the optional ingredients can be added in any suitable amount.
  • Nutritional compositions of the present disclosure may contain a carbohydrate source.
  • Any carbohydrate source conventionally found in nutritional compositions such as lactose, saccharose, maltodextrin, starch and mixtures thereof may be used although the preferred source of carbohydrates is lactose.
  • the carbohydrate source contributes between 35% and 60% of the total energy of the nutritional compositions.
  • Nutritional compositions of the present disclosure may also contain a source of lipids in addition to the lipids from the encapsulated bitter peptides.
  • the lipid source may be any lipid or fat which is suitable for use in nutritional compositions.
  • Sources of fat include, but are not limited to, high oleic sunflower oil and high oleic safflower oil.
  • the essential fatty acids linoleic and ⁇ -linolenic acid may also be added as may small amounts of oils containing high quantities of preformed arachidonic acid and docosahexaenoic acid such as fish oils or microbial oils.
  • the fat content is preferably such as to contribute between about 10% and about 10% of the total energy of the nutritional compositions.
  • the nutritional compositions further include a source of ⁇ -3 fatty acids and/or a source of ⁇ -6 fatty acids.
  • the source of ⁇ -3 fatty acids may be selected from the group consisting of fish oil, krill, plant sources containing ⁇ -3 fatty acids, flaxseed, walnut, algae, or combinations thereof.
  • the ⁇ -3 fatty acids may be selected from the group consisting of ⁇ -linolenic acid ("ALA”), docosahexaenoic acid (“DHA”), eicosapentaenoic acid (“EPA”), or combinations thereof.
  • the source of ⁇ -6 fatty acids may be selected from the group consisting of vegetable oils (e.g.
  • sunflower sassflower, soybean, corn, sesame, cottonseed, grapeseed, palm, primerose, borage and walnut
  • nuts e.g. walnuts, almonds and cashews
  • seeds e.g. flax, hemp, sunflower, sesame, pine nuts, black current and pumpkin
  • the nutritional compositions can include at least one nucleotide selected from the group consisting of a subunit of deoxyribonucleic acid (“DNA”), a subunit of ribonucleic acid (“RNA”), polymeric forms of DNA and RNA, yeast RNA, or combinations thereof.
  • the at least one nucleotide is an exogenous nucleotide.
  • the nutritional compositions further include a phytonutrient selected from the group consisting of flavanoids, allied phenolic compounds, polyphenolic compounds, terpenoids, alkaloids, sulphur-containing compounds, or combinations thereof.
  • the phytonutrient may be selected from the group consisting of carotenoids, plant sterols, quercetin, curcumin, limonin, or combinations thereof.
  • the nutritional compositions can further include a source of protein in addition to the encapsulated bitter peptides and/or the remainder of the hydrolysate.
  • a source of protein in addition to the encapsulated bitter peptides and/or the remainder of the hydrolysate.
  • Any suitable dietary protein may be used, for example animal proteins, such as dairy protein, meat protein and egg protein; or vegetable proteins, such as soy protein, wheat protein, rice protein, pea protein, corn protein, canola protein, oat protein, potato protein, peanut protein, and any proteins derived from beans, buckwheat or lentils.
  • the dairy based proteins may be casein, caseinates, casein hydrolysate, whey, whey hydrolysates, whey concentrates, whey isolates, milk protein concentrate, milk protein isolate, milk protein isolate, or combinations thereof. Dairy proteins, such as casein and whey, and/or soy proteins may be preferred for some applications.
  • the protein source contributes between 15% and 35%
  • the nutritional compositions can further include a probiotic.
  • Probiotics are food-grade microorganisms (alive, including semi-viable or weakened, and/or non-replicating), metabolites, microbial cell preparations or components of microbial cells that could confer health benefits on the host when administered in adequate amounts, more specifically, that beneficially affect a host by improving its intestinal microbial balance, leading to effects on the health or well-being of the host. See Salminen S., et al., "Probiotics: how should they be defined?," Trends Food Sci. Technol., 10, 107-10 (1999 ). In general, it is believed that these micro-organisms inhibit or influence the growth and/or metabolism of pathogenic bacteria in the intestinal tract. The probiotics may also activate the immune function of the host.
  • Non-limiting examples of probiotics include Aerococcus, Aspergillus, Bacteroides, Bifidobacterium, Candida, Clostridium, Debaromyces, Enterococcus, Fusobacterium, Lactobacillus, Lactococcus, Leuconostoc, Melissococcus, Micrococcus, Mucor, Oenococcus, Pediococcus, Penicillium, Peptostrepococcus, Pichia, Propionibacterium, Pseudocatenulatum, Rhizopus, Saccharomyces, Staphylococcus, Streptococcus, Torulopsis, Weissella, or combinations thereof.
  • the nutritional compositions further include an amino acid selected from the group consisting of alanine, arginine, asparagine, aspartate, cysteine, glutamate, glutamine, glycine, histidine, hydroxyproline, hydroxyserine, hydroxytyrosine, hydroxylysine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine, valine, or combinations thereof.
  • an amino acid selected from the group consisting of alanine, arginine, asparagine, aspartate, cysteine, glutamate, glutamine, glycine, histidine, hydroxyproline, hydroxyserine, hydroxytyrosine, hydroxylysine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, taurine, threon
  • the nutritional compositions further include an antioxidant.
  • antioxidants include astaxanthin, carotenoids, coenzyme Q10 ("CoQ10"), flavonoids, glutathione, Goji (wolfberry), hesperidin, lactowolfberry, lignan, lutein, lycopene, polyphenols, selenium, vitamin A, vitamin C, vitamin E, zeaxanthin, and combinations thereof.
  • the nutritional compositions further include a vitamin selected from the group consisting of vitamin A, Vitamin B1 (thiamine), Vitamin B2 (riboflavin), Vitamin B3 (niacin or niacinamide), Vitamin B5 (pantothenic acid), Vitamin B6 (pyridoxine, pyridoxal, or pyridoxamine, or pyridoxine hydrochloride), Vitamin B7 (biotin), Vitamin B9 (folic acid), and Vitamin B12 (various cobalamins; commonly cyanocobalamin in vitamin supplements), vitamin C, vitamin D, vitamin E, vitamin K, K1 and K2 (i.e., MK-4, MK-7), folic acid, biotin, or combinations thereof.
  • a vitamin selected from the group consisting of vitamin A, Vitamin B1 (thiamine), Vitamin B2 (riboflavin), Vitamin B3 (niacin or niacinamide), Vitamin B5 (pantothenic acid), Vitamin B6 (pyridoxine, pyridoxal, or pyridox
  • the nutritional compositions further include a mineral selected from the group consisting of boron, calcium, chromium, copper, iodine, iron, magnesium, manganese, molybdenum, nickel, phosphorus, potassium, selenium, silicon, tin, vanadium, zinc, or combinations thereof.
  • Minerals may be added in salt form. The presence and amounts of specific minerals and other vitamins will vary depending on the intended population.
  • the nutritional composition includes branched chain fatty acids that are present in the nutritional composition in an amount from about 6.25 mg to about 12.5 mg/100 g nutritional composition and assuming the nutritional composition includes 1,600 grams and is a complete feeding for a day for an adult.
  • the nutritional compositions may be provided in an amount to provide from about 100 mg to about 1,500 mg of branched chain fatty acids per day.
  • the nutritional compositions may include from about 0.5% to about 5% branched chain fatty acids by weight of total fatty acids.
  • the nutritional compositions also include a prebiotic.
  • a prebiotic is a food substance that selectively promotes the growth of beneficial bacteria or inhibits the growth or mucosal adhesion of pathogenic bacteria in the intestines. They are not inactivated in the stomach and/or upper intestine or absorbed in the gastrointestinal tract of the person ingesting them, but they are fermented by the gastrointestinal microflora and/or by probiotics.
  • Prebiotics are, for example, defined by Glenn Gibson et al., "Dietary Modulation of the Human Colonic Microbiota: Introducing the Concept of Prebiotics," J. Nutr., 125: 1401-1412 (1995 ).
  • Non-limiting examples of prebiotics include acacia gum, alpha glucan, arabinogalactans, beta glucan, dextrans, fructooligosaccharides, fucosyllactose, galactooligosaccharides, galactomannans, gentiooligosaccharides, glucooligosaccharides, guar gum, inulin, isomaltooligosaccharides, lactoneotetraose, lactosucrose, lactulose, levan, maltodextrins, milk oligosaccharides, partially hydrolyzed guar gum, pecticoligosaccharides, resistant starches, retrograded starch, sialooligosaccharides, sialyllactose, soyoligosaccharides, sugar alcohols, xylooligosaccharides, or their hydrolysates, or combinations thereof.
  • the nutritional composition can be a synbiotic that contains both a prebiotic and a probiotic that work together to improve the microflora of the intestine.
  • Samples were prepared with milk fat, cocoa fat or a mixture of medium chain triglycerides (MCT) and soy lecithin. Each of the oil/fats were added at an amount of 4% by weight to the 10% HyprolTM 3315 solution before extraction. Thirteen trained panelists ranked the samples from the least bitter (rank 1) to the most bitter (rank 4). As shown in Figure 1 , the cocoa fat sample was slightly less bitter than the reference, and the hydrolysates extracted with milk fat and the mixture of MCT/soy lecithin were perceived as significantly less bitter than the reference. A Friedman test was performed on the results (global risk 5%) and concluded that the perceived decrease in bitterness relative to the control for the milk fat and MCT/soy fat extracts was statistically significant.
  • MCT medium chain triglycerides
  • organogels were formed by dispersing HyprolTM 3315 in sunflower oil and then adding a monoglyceride gelator (DimodanTM). After gellation, the bitterness of reconstituted solutions of 10% HyprolTM 3315 were significantly reduced, meaning that the hydrophobic bitter peptides were encapsulated in organogel and were not released from organogel in water.
  • DimodanTM monoglyceride gelator

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Claims (7)

  1. Nahrungsmittelzusammensetzung, umfassend bittere Peptide, die in einer Struktur eingekapselt sind, wobei die Struktur ein Organogel ist, das ein Öl oder geschmolzenes Fett und einen Gelator umfasst, der ausgewählt ist aus der Liste bestehend aus Phospholipiden, Lecithin, Monoglycerid, amphiphilen Peptiden, Sorbitanmonostearat, Mono-, Di- und/oder Triacyglycerinen, Fettsäuren, Fettalkohol, Wachs, Phytosterol und/oder Kombinationen davon.
  2. Verfahren zum Einkapseln von bitteren Peptiden, wobei das Verfahren die folgenden Schritte umfasst:
    Bilden einer Emulsion, die eine Wasserphase umfasst, die ein Proteinhydrolysat und eine Ölphase enthält, die mindestens eines von einem Öl oder einem geschmolzenen Fett umfasst; und
    Zugeben eines Gelators zu der Emulsion, um ein Organogel zu bilden, nachdem die bitteren Peptide aus dem Proteinhydrolysat in Öltröpfchen in die Ölphase migrieren, wobei die Zugabe des Gelators die bitteren Peptide in dem Organogel einfängt.
  3. Verfahren nach Anspruch 2, umfassend die Hydrolyse eines Proteins, um eine Lösung zu bilden, die das Proteinhydrolysat umfasst, wobei die bitteren Peptide in dem Organogel derart in Reihe eingefangen werden, dass die Emulsion nach der Hydrolyse direkt in der Lösung gebildet wird, die das Proteinhydrolysat umfasst.
  4. Verfahren nach einem der Ansprüche 2 oder 3, wobei das Proteinhydrolysat ein Milchproteinhydrolysat ist.
  5. Verfahren nach einem der Ansprüche 2 oder 3, wobei die Hydrolyse nicht bittere Peptide bildet, und wobei mindestens ein Anteil der nicht bitteren Peptide nicht in der Ölphase eingefangen ist.
  6. Bittere Peptide, die in einer Struktur eingekapselt sind, wobei die Struktur ein Organogel ist.
  7. Verfahren zum Bereitstellen von Nahrung für eine Person, umfassend das Verabreichen einer Nahrungsmittelzusammensetzung, die bittere Peptide aus Proteinhydrolysat umfasst, an die Person, wobei die bitteren Peptide in einer Struktur eingekapselt sind, wobei die Struktur ein Organogel ist.
EP13779563.9A 2012-10-25 2013-10-17 Eingekapselte bittere peptide, verfahren zum einkapseln bittere peptide und nahrungszusammensetzungen mit verkapselten bitteren peptiden Active EP2911530B1 (de)

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Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109845877B (zh) * 2017-11-30 2022-07-12 内蒙古伊利实业集团股份有限公司 一种水解蛋白脱苦组合物及其产品、制备和应用
JP2020184911A (ja) * 2019-05-13 2020-11-19 日清オイリオグループ株式会社 Ｈｍｂ由来の異味抑制剤、ｈｍｂ由来の異味抑制剤を含む飲食品、及びｈｍｂ由来の異味の抑制方法
CN113498864A (zh) * 2021-06-21 2021-10-15 内蒙古农业大学 一种驼乳多肽纳米颗粒口服液及其制备方法
CN114680332B (zh) * 2022-03-11 2023-08-18 杭州佰倍优生物科技有限公司 一种运载苦味物质的油包水型高内相乳液及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3493385A (en) 1965-07-19 1970-02-03 Corn Products Co Process for the removal of undesirable flavor substances from protein hydrolyzates
DE69732239T2 (de) 1996-05-10 2005-12-22 Unilever N.V. Flüssige fettverbindung enthaltende zusammensetzung
WO2006084573A1 (en) 2005-02-09 2006-08-17 Unilever N.V. Food products comprising hydrolysed milk solids with improved taste
US20100215731A1 (en) 2009-02-20 2010-08-26 Maastricht University Method for improving cartilage repair and/or preventing cartilage degeneration in a joint

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5223263A (en) * 1988-07-07 1993-06-29 Vical, Inc. Liponucleotide-containing liposomes
EP0321603A1 (de) 1987-12-23 1989-06-28 Societe Des Produits Nestle S.A. Verfahren zur Herstellung eines Molke-Eiweisshydrolysates und eines hypoallergenen Nahrungsmittels
FR2625651B1 (fr) * 1988-01-08 1994-01-21 Bioeurope Procede d'elimination de l'amertume d'hydrolysats de proteines et produit obtenu
JPH0283031A (ja) * 1988-09-20 1990-03-23 Lion Corp マイクロカプセルの製造方法
US5300302A (en) * 1990-10-04 1994-04-05 Nestec S.A. Pharmaceutical composition in gel form in a dispensing package
JP3370809B2 (ja) * 1994-12-27 2003-01-27 花王株式会社 食品用組成物、苦味低減化法、及び栄養食品
JPH09162A (ja) * 1995-06-16 1997-01-07 Kao Corp 苦みの低減された蛋白質加水分解物の製造法
DE69616978T2 (de) * 1996-03-27 2002-05-29 Societe Des Produits Nestle S.A., Vevey Protein-verkapselte Teilchen aus einer Polysaccharid-enthaltender Dispersion
DK0974366T3 (da) * 1997-03-28 2007-01-29 Eisai Co Ltd Orale, farmaceutiske præparater med nedsat bitterhed ved maskering
SE0102933D0 (sv) * 2001-09-04 2001-09-04 Lipocore Holding Ab Lipid carrier
KR100950143B1 (ko) * 2002-07-29 2010-03-30 오츠카 세이야쿠 가부시키가이샤 겔상 음료 조성물
JP4533185B2 (ja) * 2005-02-24 2010-09-01 花王株式会社 固体脂質粒子製剤
JP4987261B2 (ja) * 2005-07-13 2012-07-25 株式会社 メドレックス ゲル状経口製剤
JP4634886B2 (ja) * 2005-08-03 2011-02-16 金秀バイオ株式会社 高機能性健康食品の苦味低減化方法、及び低苦味組成物
EP1954384A1 (de) * 2005-11-23 2008-08-13 Nestec S.A. Öl-in-wasser-emulsion zur bildung neuer produktkonsistenzen
CA2645073A1 (en) * 2006-03-08 2007-09-13 Nuviance, Inc. Transdermal drug delivery compositions and topical compositions for application on the skin
EP2024076A1 (de) * 2006-05-22 2009-02-18 Nizo Food Research B.V. Proteinverkapselte partikel
EP1897451A1 (de) * 2006-09-08 2008-03-12 SHS International Ltd. Geschmacksneutraler Lebensmittelzusatz enthaltend Aminosäure
WO2008130220A1 (en) * 2007-04-20 2008-10-30 N.V. Nutricia Process for dispersing amino acids
CN101156661A (zh) * 2007-11-12 2008-04-09 浙江大学 一种蛋白酶解物的脱苦方法
NL2002046C (en) * 2008-10-01 2010-04-02 Friesland Brands Bv Double emulsion and method to produce such.
ES2548629T3 (es) * 2010-08-24 2015-10-19 Abbott Laboratories Productos nutritivos que tienen propiedades organolépticas mejoradas
JP5717422B2 (ja) * 2010-11-30 2015-05-13 株式会社パイロットコーポレーション ゲル状組成物の製造方法
CN102204620B (zh) * 2011-05-10 2012-12-26 华南理工大学 无苦味蛋白肽的制备方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3493385A (en) 1965-07-19 1970-02-03 Corn Products Co Process for the removal of undesirable flavor substances from protein hydrolyzates
DE69732239T2 (de) 1996-05-10 2005-12-22 Unilever N.V. Flüssige fettverbindung enthaltende zusammensetzung
WO2006084573A1 (en) 2005-02-09 2006-08-17 Unilever N.V. Food products comprising hydrolysed milk solids with improved taste
US20100215731A1 (en) 2009-02-20 2010-08-26 Maastricht University Method for improving cartilage repair and/or preventing cartilage degeneration in a joint

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
"Sunflower oil", WIKIPEDIA, 19 October 2017 (2017-10-19), XP055435662
BARBOSA ET AL.: "Papain hydrolysates of casein: molecular weight profile and encapsu- lation in lipospheres", JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, vol. 84, 2004, pages 1891 - 1900, XP055435667
FATHI ET AL.: "Nanoencapsulation of food ingredients using lipid based delivery sys- tems", TRENDS IN FOOD SCIENCE & TECHNOLOGY, vol. 23, 2012, pages 13 - 27, XP028347765
FAVARO-TRINDADE ET AL.: "The use of spray drying technology to reduce bitter taste of casein hydrolysate", FOOD HYDROCOLLOIDS, vol. 24, 2010, pages 336 - 340, XP026879457
TARUN ET AL.: "Organogels: Advanced and novel drug delivery system", INTERNATIONAL RESEARCH JOURNAL OF PHARMACY, vol. 2, no. 12, 2011, pages 15 - 21, XP055435653
VINTILOIU ET AL.: "Organogels and their use in drug delivery - A review", JOURNAL OF CONTROLLED RELEASE, vol. 125, 2008, pages 179 - 192, XP022432121

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JP2015536136A (ja) 2015-12-21
ES2618204T3 (es) 2017-06-21
CA2887046C (en) 2021-08-31
WO2014063985A2 (en) 2014-05-01
US20150290131A1 (en) 2015-10-15
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CN104703487B (zh) 2017-05-17
BR112015009002B1 (pt) 2020-02-27
DK2911530T3 (en) 2017-03-20
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AU2013336907A1 (en) 2015-04-23

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